Housatonic Holiday Homes from €130: Search Top House Rentals

A river flanked by autumn-colored trees and residential areas.

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Our top choices for Housatonic holiday homes

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

1. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

includes taxes & fees

8 Oct - 9 Oct

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

2. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

3. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

4. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveller

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

5. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mark M.

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

6. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

7. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

includes taxes & fees

4 Oct - 5 Oct

A camping setup with a metal chair and a table by a river in a forest.

8. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

includes taxes & fees

4 Oct - 5 Oct

A spacious living room with a dining area, a kitchen, and a large window.

9. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

includes taxes & fees

5 Oct - 6 Oct

A modern living room with a sofa, armchair, coffee table, and TV.

10. Spacious Central Berkshires Home for Groups

Lee

Beth S.

includes taxes & fees

5 Oct - 6 Oct

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

11. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

includes taxes & fees

7 Oct - 8 Oct

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

12. Ellie’s Overlook, best view in the Berkshires!

Richmond

includes taxes & fees

6 Oct - 7 Oct

A hot tub with a string of lights above it, set against a dark night sky.

13. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

includes taxes & fees

14 Oct - 15 Oct

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

14. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

28 Oct - 29 Oct